JP5340287B2 - 4−フルオロ置換3−オキソ−アルカン酸のエステル類の調製方法 - Google Patents
4−フルオロ置換3−オキソ−アルカン酸のエステル類の調製方法 Download PDFInfo
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- JP5340287B2 JP5340287B2 JP2010520581A JP2010520581A JP5340287B2 JP 5340287 B2 JP5340287 B2 JP 5340287B2 JP 2010520581 A JP2010520581 A JP 2010520581A JP 2010520581 A JP2010520581 A JP 2010520581A JP 5340287 B2 JP5340287 B2 JP 5340287B2
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- oxo
- esters
- difluoro
- substituted
- fluoro
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- 150000002148 esters Chemical class 0.000 title claims abstract description 25
- 239000002253 acid Substances 0.000 title claims abstract description 10
- 150000007513 acids Chemical class 0.000 title claims abstract description 8
- 238000000034 method Methods 0.000 title claims description 20
- 238000002360 preparation method Methods 0.000 title description 8
- 230000032050 esterification Effects 0.000 claims abstract description 14
- 238000005886 esterification reaction Methods 0.000 claims abstract description 14
- CCGKOQOJPYTBIH-UHFFFAOYSA-N ethenone Chemical compound C=C=O CCGKOQOJPYTBIH-UHFFFAOYSA-N 0.000 claims abstract description 12
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 14
- 150000001875 compounds Chemical class 0.000 claims description 6
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 claims description 4
- 125000000217 alkyl group Chemical group 0.000 claims description 4
- 238000007539 photo-oxidation reaction Methods 0.000 claims description 4
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 3
- 125000004432 carbon atom Chemical group C* 0.000 claims description 3
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 3
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 3
- 239000001301 oxygen Substances 0.000 claims description 3
- 229910052760 oxygen Inorganic materials 0.000 claims description 3
- 229910052725 zinc Inorganic materials 0.000 claims description 3
- 239000011701 zinc Substances 0.000 claims description 3
- 125000001153 fluoro group Chemical group F* 0.000 claims description 2
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 2
- 125000004429 atom Chemical group 0.000 claims 1
- 239000003795 chemical substances by application Substances 0.000 claims 1
- 238000005191 phase separation Methods 0.000 claims 1
- HQZSNVHMLLTTRA-UHFFFAOYSA-N 4,4-difluoro-3-oxobutanoic acid Chemical compound OC(=O)CC(=O)C(F)F HQZSNVHMLLTTRA-UHFFFAOYSA-N 0.000 abstract description 11
- NGNBDVOYPDDBFK-UHFFFAOYSA-N 2-[2,4-di(pentan-2-yl)phenoxy]acetyl chloride Chemical compound CCCC(C)C1=CC=C(OCC(Cl)=O)C(C(C)CCC)=C1 NGNBDVOYPDDBFK-UHFFFAOYSA-N 0.000 abstract description 5
- 239000007795 chemical reaction product Substances 0.000 abstract description 4
- 238000007259 addition reaction Methods 0.000 abstract description 3
- AZPWOLJQERBBBM-UHFFFAOYSA-N 2-chloro-2,2-difluoroacetyl chloride Chemical compound FC(F)(Cl)C(Cl)=O AZPWOLJQERBBBM-UHFFFAOYSA-N 0.000 description 8
- 238000006243 chemical reaction Methods 0.000 description 7
- 239000000460 chlorine Substances 0.000 description 7
- 239000011541 reaction mixture Substances 0.000 description 7
- 229910052801 chlorine Inorganic materials 0.000 description 6
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 5
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 3
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- -1 carboxylic acid chlorides Chemical class 0.000 description 3
- 125000004494 ethyl ester group Chemical group 0.000 description 3
- 239000002904 solvent Substances 0.000 description 3
- KOPFEFZSAMLEHK-UHFFFAOYSA-N 1h-pyrazole-5-carboxylic acid Chemical compound OC(=O)C=1C=CNN=1 KOPFEFZSAMLEHK-UHFFFAOYSA-N 0.000 description 2
- BWAFLSFSMHXWMF-UHFFFAOYSA-N 4-chloro-4,4-difluoro-3-oxobutanoic acid Chemical compound OC(=O)CC(=O)C(F)(F)Cl BWAFLSFSMHXWMF-UHFFFAOYSA-N 0.000 description 2
- XWAUUOIYUMIQCO-UHFFFAOYSA-N 4-chloro-4,4-difluoro-3-oxobutanoyl chloride Chemical compound FC(F)(Cl)C(=O)CC(Cl)=O XWAUUOIYUMIQCO-UHFFFAOYSA-N 0.000 description 2
- XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
- 239000005388 borosilicate glass Substances 0.000 description 2
- 125000001309 chloro group Chemical group Cl* 0.000 description 2
- 238000004821 distillation Methods 0.000 description 2
- 239000000417 fungicide Substances 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- 239000007791 liquid phase Substances 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- 229910052751 metal Inorganic materials 0.000 description 2
- 239000002184 metal Substances 0.000 description 2
- 239000003960 organic solvent Substances 0.000 description 2
- 238000007254 oxidation reaction Methods 0.000 description 2
- 239000012071 phase Substances 0.000 description 2
- 239000000047 product Substances 0.000 description 2
- 230000005855 radiation Effects 0.000 description 2
- 239000007858 starting material Substances 0.000 description 2
- 150000003512 tertiary amines Chemical class 0.000 description 2
- SCYULBFZEHDVBN-UHFFFAOYSA-N 1,1-Dichloroethane Chemical compound CC(Cl)Cl SCYULBFZEHDVBN-UHFFFAOYSA-N 0.000 description 1
- FQAMAOOEZDRHHB-UHFFFAOYSA-N 1,2,2-trichloro-1,1-difluoroethane Chemical compound FC(F)(Cl)C(Cl)Cl FQAMAOOEZDRHHB-UHFFFAOYSA-N 0.000 description 1
- UBDSMLOYYGZYOZ-UHFFFAOYSA-N 4,4-difluoro-3-oxobutanoic acid 1,2,2-trichloro-1,1-difluoroethane Chemical compound FC(F)(Cl)C(Cl)Cl.OC(=O)CC(=O)C(F)F UBDSMLOYYGZYOZ-UHFFFAOYSA-N 0.000 description 1
- KPHUEJPKXUQOCU-UHFFFAOYSA-N 4,5,5,5-tetrafluoro-3-oxopentanoic acid Chemical compound OC(=O)CC(=O)C(F)C(F)(F)F KPHUEJPKXUQOCU-UHFFFAOYSA-N 0.000 description 1
- LEDWOGXMWHKIOE-UHFFFAOYSA-N 4-chloro-2,2-difluoro-3-oxobutanoic acid Chemical compound OC(=O)C(F)(F)C(=O)CCl LEDWOGXMWHKIOE-UHFFFAOYSA-N 0.000 description 1
- IAZJIGNPEMCLMA-UHFFFAOYSA-N 4-chloro-2,2-difluoro-3-oxobutanoyl chloride Chemical compound ClC(=O)C(F)(F)C(=O)CCl IAZJIGNPEMCLMA-UHFFFAOYSA-N 0.000 description 1
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 1
- IGQNDARULCASRN-UHFFFAOYSA-N Fluxapyroxad (bas 700 f)-tp cscd465008 Chemical class OC(=O)C1=CNN=C1C(F)F IGQNDARULCASRN-UHFFFAOYSA-N 0.000 description 1
- CYTYCFOTNPOANT-UHFFFAOYSA-N Perchloroethylene Chemical group ClC(Cl)=C(Cl)Cl CYTYCFOTNPOANT-UHFFFAOYSA-N 0.000 description 1
- WTKZEGDFNFYCGP-UHFFFAOYSA-N Pyrazole Chemical compound C=1C=NNC=1 WTKZEGDFNFYCGP-UHFFFAOYSA-N 0.000 description 1
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
- 150000001338 aliphatic hydrocarbons Chemical class 0.000 description 1
- 150000008064 anhydrides Chemical class 0.000 description 1
- 229910052787 antimony Inorganic materials 0.000 description 1
- VMPVEPPRYRXYNP-UHFFFAOYSA-I antimony(5+);pentachloride Chemical compound Cl[Sb](Cl)(Cl)(Cl)Cl VMPVEPPRYRXYNP-UHFFFAOYSA-I 0.000 description 1
- 229910052786 argon Inorganic materials 0.000 description 1
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 150000001656 butanoic acid esters Chemical class 0.000 description 1
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- 150000008280 chlorinated hydrocarbons Chemical class 0.000 description 1
- 150000001805 chlorine compounds Chemical class 0.000 description 1
- 239000013065 commercial product Substances 0.000 description 1
- 238000009833 condensation Methods 0.000 description 1
- 230000005494 condensation Effects 0.000 description 1
- 239000000039 congener Substances 0.000 description 1
- 239000012043 crude product Substances 0.000 description 1
- 239000000645 desinfectant Substances 0.000 description 1
- 125000004185 ester group Chemical group 0.000 description 1
- WBJINCZRORDGAQ-UHFFFAOYSA-N formic acid ethyl ester Natural products CCOC=O WBJINCZRORDGAQ-UHFFFAOYSA-N 0.000 description 1
- 230000000855 fungicidal effect Effects 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- 150000008282 halocarbons Chemical class 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 1
- 239000011261 inert gas Substances 0.000 description 1
- 239000000543 intermediate Substances 0.000 description 1
- 238000002955 isolation Methods 0.000 description 1
- HDZGCSFEDULWCS-UHFFFAOYSA-N monomethylhydrazine Chemical compound CNN HDZGCSFEDULWCS-UHFFFAOYSA-N 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 230000003647 oxidation Effects 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 229910052715 tantalum Inorganic materials 0.000 description 1
- 229950011008 tetrachloroethylene Drugs 0.000 description 1
- GKASDNZWUGIAMG-UHFFFAOYSA-N triethyl orthoformate Chemical compound CCOC(OCC)OCC GKASDNZWUGIAMG-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C67/00—Preparation of carboxylic acid esters
- C07C67/14—Preparation of carboxylic acid esters from carboxylic acid halides
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C51/00—Preparation of carboxylic acids or their salts, halides or anhydrides
- C07C51/58—Preparation of carboxylic acid halides
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C67/00—Preparation of carboxylic acid esters
- C07C67/30—Preparation of carboxylic acid esters by modifying the acid moiety of the ester, such modification not being an introduction of an ester group
- C07C67/317—Preparation of carboxylic acid esters by modifying the acid moiety of the ester, such modification not being an introduction of an ester group by splitting-off hydrogen or functional groups; by hydrogenolysis of functional groups
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Description
RCFClC(O)Cl (I)
(式中、Rは、C2F5、CF3、またはFである)
の化合物をケテンと反応させて付加物を形成し、エステル化工程においてこの付加物を反応させて対応するエステルを形成し、その後に水素化脱塩素して式(II):
RCFHC(O)CH2C(O)OR1 (II)
(式中、Rは上記定義のとおりであり、R1は、1個〜4個の炭素原子を有するアルキル基または1個または複数のフッ素原子により置換されている1個〜4個の炭素原子を有するアルキル基である)
の化合物を形成することにより調製される。好ましくは、R1は、メチル、エチル、またはプロピルである。
商業的供給源からの1,1−ジフルオロ−1,2,2−トリクロロエタンを、米国特許第5,569,782号明細書(特許文献8)に示されている条件下で、約290nmより短い波長の光に対するフィルターとしてホウケイ酸ガラスを用いた装置において、塩素の非存在下で酸素と反応させる。
Claims (7)
- 式(I):
RCFClC(O)Cl (I)
(式中、Rは、C2F5、CF3、またはFである)
の化合物をケテンと反応させて付加物を形成し、エステル化工程において前記付加物を反応させて対応するエステルを形成し、その後に水素化脱塩素を行って式(II):
RCFHC(O)CH2C(O)OR1 (II)
(式中、Rは上記定義のとおりであり、R1は、1個〜4個の炭素原子を有するアルキル基、または1個または複数のフッ素原子により置換されている1個〜4個の炭素原子を有するアルキル基である)
の化合物を形成することにより、4−フルオロ置換3−オキソ−アルカン酸のエステルを調製するための方法。 - RがFである、請求項1に記載の方法。
- R1が、メチル、エチル、またはプロピルである、請求項1または2に記載の方法。
- R 1 がエチルである、請求項3に記載の方法。
- 前記エステル化工程が、塩基または相分離剤の非存在下で行われる、請求項1に記載の方法。
- 前記化合物RCFClC(O)Clが、RCFClCHCl2と酸素との光酸化により調製され、ここで、Rは上記定義のとおりである、請求項1に記載の方法。
- 前記水素化脱塩素が、エステル化工程において用いられたアルコールの存在下で前記エステルを亜鉛と反応させることにより行われる、請求項1に記載の方法。
Applications Claiming Priority (3)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
EP07114439 | 2007-08-16 | ||
EP07114439.8 | 2007-08-16 | ||
PCT/EP2008/060674 WO2009021987A1 (en) | 2007-08-16 | 2008-08-14 | Process for the preparation of esters of 4-fluorosubstituted 3-oxo-alcanoic acids |
Publications (2)
Publication Number | Publication Date |
---|---|
JP2010536730A JP2010536730A (ja) | 2010-12-02 |
JP5340287B2 true JP5340287B2 (ja) | 2013-11-13 |
Family
ID=38887418
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
JP2010520581A Expired - Fee Related JP5340287B2 (ja) | 2007-08-16 | 2008-08-14 | 4−フルオロ置換3−オキソ−アルカン酸のエステル類の調製方法 |
Country Status (5)
Country | Link |
---|---|
US (1) | US8481778B2 (ja) |
EP (1) | EP2181087B1 (ja) |
JP (1) | JP5340287B2 (ja) |
CN (2) | CN105732376A (ja) |
WO (1) | WO2009021987A1 (ja) |
Families Citing this family (10)
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US8481778B2 (en) | 2007-08-16 | 2013-07-09 | Solvay (Societe Anonyme) | Process for the preparation of esters of 4-fluorosubstituted 3-oxo-alcanoic acids |
WO2010094746A2 (en) | 2009-02-19 | 2010-08-26 | Solvay Fluor Gmbh | Compositions of esters of fluorosubstituted alcanoic acids |
TWI562985B (en) * | 2010-07-13 | 2016-12-21 | Lonza Ag | Process for the preparation of enolate salts of 4-fluoro-2-hydroxymethylene-3-oxobutyrates |
WO2012010692A1 (en) | 2010-07-23 | 2012-01-26 | Solvay Sa | Process for the preparation of esters of 1-substituted-3-fluoroalkyl-pyrazole-4-carboxylic acids |
WO2012025469A1 (en) | 2010-08-24 | 2012-03-01 | Solvay Sa | Improved process for the preparation of esters of 1-h-pyrazole-4-carboxylic acids |
WO2012055864A1 (en) | 2010-10-27 | 2012-05-03 | Solvay Sa | Process for the preparation of pyrazole-4-carboxamides |
CN102344351B (zh) * | 2011-07-29 | 2013-12-25 | 中山大学 | 芳基取代查尔酮类化合物及其制备方法和应用 |
EP2671874B1 (en) | 2012-06-06 | 2016-01-13 | Solvay Sa | Preparation of esters of 1-substituted-3-fluoroalkyl-pyrazole-4-carboxylic acids |
CN104710350B (zh) * | 2015-03-17 | 2017-07-04 | 湖北犇星农化有限责任公司 | 一种三氯吡啶醇钠的合成方法 |
CN108884051A (zh) | 2016-01-28 | 2018-11-23 | 索尔维公司 | 卤素取代的二酮化合物、吡唑化合物及用于制造吡唑化合物的方法 |
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DE102006039909A1 (de) | 2006-08-25 | 2008-03-13 | Bayer Cropscience Ag | Verfahren zum Herstellen von 3-Dihalomethyl-pyrazol-4-carbonsäurederivaten |
DE102007005296A1 (de) | 2007-02-02 | 2008-08-07 | Bayer Cropscience Ag | Verfahren zum Herstellen von Dihaloacetessigsäurealkylestern |
US8481778B2 (en) | 2007-08-16 | 2013-07-09 | Solvay (Societe Anonyme) | Process for the preparation of esters of 4-fluorosubstituted 3-oxo-alcanoic acids |
EP2133341A1 (de) | 2008-02-25 | 2009-12-16 | Bayer CropScience AG | Verfahren zur regioselektiven Synthese von 1-Alkyl-3-haloalkyl-pyrazol-4-carbonsäure-Derivaten |
EP2100883A1 (de) | 2008-03-10 | 2009-09-16 | Bayer CropScience AG | Verfahren zur regioselektiven Synthese von 1-Alkyl-3-haloalkyl-pyrazol-4carbonsäure-Derivaten |
KR20110004903A (ko) | 2008-05-08 | 2011-01-14 | 바스프 에스이 | 아릴카르복스아미드의 제조 방법 |
CN102026982A (zh) | 2008-05-14 | 2011-04-20 | 先正达参股股份有限公司 | 制备酰胺的方法 |
AU2009282567B2 (en) | 2008-08-20 | 2014-10-02 | Merck Sharp & Dohme Corp. | Substituted pyridine and pyrimidine derivatives and their use in treating viral infections |
KR20100116334A (ko) | 2009-04-22 | 2010-11-01 | 김병구 | 한약재를 이용한 발모제의 제조방법 및 그에 의해 제조된 발모제 |
CN102471202B (zh) | 2009-07-06 | 2015-10-07 | 索尔维公司 | 在溶剂存在下制造烯酮的卤化前体的方法 |
EP2451764B1 (en) | 2009-07-06 | 2016-01-13 | Solvay Sa | Process for the manufacture of alkenones |
CN102471201A (zh) | 2009-07-06 | 2012-05-23 | 索尔维公司 | 用于在特定条件下制造烯酮的卤化前体的方法 |
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US8481778B2 (en) | 2013-07-09 |
EP2181087A1 (en) | 2010-05-05 |
CN101801906A (zh) | 2010-08-11 |
JP2010536730A (ja) | 2010-12-02 |
CN105732376A (zh) | 2016-07-06 |
US20110301378A1 (en) | 2011-12-08 |
EP2181087B1 (en) | 2015-10-14 |
WO2009021987A1 (en) | 2009-02-19 |
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